Flame retardant flexible polyurethane foams from novel DOPO-phosphonamidate additives

Gaan, Sabyasachi; Liang, Shuyu; Mispreuve, H.; Perler, Heribert; Naescher, Reinold; Neisius, Matthias

doi:10.1016/j.polymdegradstab.2015.01.007

Cited by 156 publications

(102 citation statements)

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“…The three novel compounds were designed in order to possess improved flame retardation potential, but also for a wide range of applications based on their higher melting points and increased stability, which are prerequisites for their use in the production of plastic materials (Buczko et al 2014; Gaan et al 2013, 2015; Neisius et al 2014; Salmeia and Gaan 2015; Salmeia et al 2015; Qiang et al 2011). In contrast to the current practice of investigating the potential harmful properties of flame retardants after their introduction into the market, we applied here a series of human in vitro screening assays to allow a fundamental toxicological classification before the production and application of halogen-free bis -DOPO compounds on an industrial scale.…”

Section: Discussionmentioning

confidence: 99%

“…In order to improve its flame retardation potential and influence its physico-chemical parameters, such as its melting point, to allow industrial application in different plastic materials, novel phosphonamidate and phosphonate and phosphinate derivatives of DOPO have been developed (Gaan et al 2009, 2013, 2015; Buczko et al 2014; Neisius et al 2014; Salmeia and Gaan 2015; Salmeia et al 2015), but have not been evaluated with respect to their toxicological potential. In the combustion process, phosphonamidate DOPO derivatives primarily act in the vapor phase by forming phosphorus-containing radical species (PO · ) (Salmeia and Gaan 2015; Salmeia et al 2015), which interact with · OH or H · radicals (Eq.…”

Section: Introductionmentioning

confidence: 99%

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Multiparameter toxicity assessment of novel DOPO-derived organophosphorus flame retardants

Hirsch

Striegl²,

Mathes

et al. 2016

Arch Toxicol

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Halogen-free organophosphorus flame retardants are considered as replacements for the phased-out class of polybrominated diphenyl ethers (PBDEs). However, toxicological information on new flame retardants is still limited. Based on their excellent flame retardation potential, we have selected three novel 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) derivatives and assessed their toxicological profile using a battery of in vitro test systems in order to provide toxicological information before their large-scale production and use. PBDE-99, applied as a reference compound, exhibited distinct neuro-selective cytotoxicity at concentrations ≥10 µM. 6-(2-((6-oxido-6H-dibenzo[c,e][1,2]oxaphosphinin-6-yl)amino)ethoxy)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide (ETA-DOPO) and 6,6′-(ethane-1,2-diylbis(oxy))bis(6H-dibenzo[c,e][1,2]oxaphosphinine-6-oxide) (EG-DOPO) displayed adverse effects at concentrations >10 µM in test systems reflecting the properties of human central and peripheral nervous system neurons, as well as in a set of non-neuronal cell types. DOPO and its derivative 6,6′-(ethane-1,2-diylbis(azanediyl))bis(6H-dibenzo[c,e][1,2]oxaphosphinine-6-oxide) (EDA-DOPO) were neither neurotoxic, nor did they exhibit an influence on neural crest cell migration, or on the integrity of human skin equivalents. The two compounds furthermore displayed no inflammatory activation potential, nor did they affect algae growth or daphnia viability at concentrations ≤400 µM. Based on the superior flame retardation properties, biophysical features suited for use in polyurethane foams, and low cytotoxicity of EDA-DOPO, our results suggest that it is a candidate for the replacement of currently applied flame retardants.Electronic supplementary materialThe online version of this article (doi:10.1007/s00204-016-1680-4) contains supplementary material, which is available to authorized users.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Multiparameter toxicity assessment of novel DOPO-derived organophosphorus flame retardants

Hirsch

Striegl²,

Mathes

et al. 2016

Arch Toxicol

Self Cite

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“…As a consequence, the flame temperature is lowered and the resultant oxides form a protective layer, on the surface of the material, limiting the movement of the volatile degradation products to the flame and oxygen to the burning material. The group of flame retardants containing phosphorus and nitrogen includes, among others, phosphaphenanthrene phosphonamidates [12], ammonium polyphosphate [13,14], polydopamine [15], triphenylphosphate [16], dimethyl methylphosphonate [17], dimethylpropanphosphonate [18], hexaphenoxy cyclotriphosphazene [19] and aluminum phosphinate [4,20,21].…”

Section: Introductionmentioning

confidence: 99%

Analysis of flammability and smoke emission of rigid polyurethane foams modified with nanoparticles and halogen-free fire retardants

Sałasińska

Borucka

Leszczyńska

et al. 2017

J Therm Anal Calorim

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Using one-step method, rigid polyurethane foams were made, modified with developed fire retardant systems containing halogen-free flame retardants and nanofillers in the form of multi-walled carbon nanotubes or nanoscale titanium dioxide. The materials were subjected to a test using a cone calorimeter and smoke-generating chamber, and selected samples were further analyzed via thermogravimetry and oxygen index. Moreover, the products of thermal degradation of selected samples were identified using gas chromatography with mass spectrometer. Conducted flammability tests confirmed the presence of a synergistic effect between the used nanofillers and halogen-free flame retardants. It has been observed that the carbonized layer, the formation of which favored the presence of nanoadditives, inhibits the combustion process. Furthermore, nanofillers influenced favorably reduction in the amount and the number of occurring products of thermal degradation.

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“…Due to the less health hazard, the flame retardants containing phosphorus/nitrogen applied in RPUF have received more attentions. According to the previous literature, some researchers used a lot of additiontype flame retardants, such as phosphaphenanthrenephosphonamidates(EDAB-DOPO) [14], ammonium polyphosphate (APP) [15,16], polydopamine (PDA) [17], expandable graphite (EG) [18e20], polyhedral oligomeric silsesquioxane (POSS) [21], triphenylphosphate (TPP) [22], dimethyl methylphosphonate (DMMP) [23e25], dimethylpropanphosphonate (DMPP) [26], hexaphenoxy-cyclotriphosphazene (HPCP) [27] and aluminium phosphinate [28]. They all can enhance the flame retardancy of RPUFs.…”

Section: Introductionmentioning

confidence: 99%

Continuous flame-retardant actions of two phosphate esters with expandable graphite in rigid polyurethane foams

Qian

Huang

et al. 2016

Polymer Degradation and Stability

102

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Flame retardant flexible polyurethane foams from novel DOPO-phosphonamidate additives

Cited by 156 publications

References 10 publications

Multiparameter toxicity assessment of novel DOPO-derived organophosphorus flame retardants

Multiparameter toxicity assessment of novel DOPO-derived organophosphorus flame retardants

Analysis of flammability and smoke emission of rigid polyurethane foams modified with nanoparticles and halogen-free fire retardants

Continuous flame-retardant actions of two phosphate esters with expandable graphite in rigid polyurethane foams

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